David Freedlander is a veteran New York City-based journalist. He writes long-form features about politics  and the arts, people and ideas, and has appeared in New York Magazine, Bloomberg, Rolling Stone, ArtNews, The Daily Beast, Newsweek and a host of other publications.

Bill de Blasio Gets Ready for a Late, Awkward Run for President

Bill de Blasio Gets Ready for a Late, Awkward Run for President

Published May 7, 2019 in

In his six years as mayor of New York, Bill de Blasio has eaten pizza with a knife and fork, refused to relinquish his Boston Red Sox fandom long enough to attend a game at Yankee Stadium, killed a groundhog, overseen the murder of a lost deer, refused to stop driving 11 miles to his favorite gym despite widespread condemnation, shown up late to a memorial for people killed in a plane crash, skipped the funeral of a city dignitary, and feuded with the governor of New York and even his own police force.

All of which is to say, the guy does things a little bit differently.

And perhaps never has that been more apparent now that the mayor, facing a field of nearly two dozen other Democrats who have been campaigning for the presidency for months, is on the cusp of jumping into the race, despite lukewarm poll numbers back home that show that over three-quarters of New York residents don’t want him to run, and without a groundswell of support from his fellow Democrats.

Although the Daily News reported on Friday that the mayor was planning to make an announcement this week, de Blasio insisted in local TV interview Monday that no decision had been made. “You can’t have an announcement before there is a decision,” he said.

According to people familiar with the mayor’s thinking, de Blasio remains committed to making a decision before the end of the month. The mayor is still in conversation with his family about the toll a run would take, but people who have spoken with him say he is leaning toward a campaign.

A de Blasio presidential campaign would be a lean operation, one centered mostly around the mayor and his immediate family. The brain trust that helped him in his come-from-behind victory when he ran for mayor in 2013 and guided his first couple of years in office has largely vanished, and as of late, the defections from his inner circle at City Hall have increased. Still, should the mayor run, his focus, people close to him said, would be on income inequality, the same issue that propelled de Blasio to a victory in his 2013 campaign for mayor.

“Here’s the truth, brothers and sisters, there’s plenty of money in the world. Plenty of money in this city,” the mayor said at his State of the City address earlier this year, in a line he has repeated elsewhere and would likely make the centerpiece of a campaign. “It’s just in the wrong hands!”

Most of the Democratic field has been campaigning, raising money, and hiring staffers for the past six months. De Blasio will enter the race not only at a standstill, but without a clear lane for his candidacy. Want an unabashed progressive as your nominee? Got a couple of those already running. Want someone with experience running a city? Got three of those too — former Denver mayor John Hickenlooper, former Newark mayor Cory Booker, and current South Bend, Indiana, mayor Pete Buttigieg. Want a middle-aged white guy? Well, first of all, what the hell is wrong with you? — and secondly, there’s no shortage of them either.

De Blasio’s inching toward announcing a run has surprised some of his closest aides and associates who fret that it will take him away from his duties back home, and play further into the narrative that he is uninterested in the job that he was elected to do. They acknowledge that in an awfully crowded field, even the six-foot-five mayor of America’s largest city will have trouble standing out.

Yet de Blasio seems determined to make his case. Friends, aides, and people familiar with his thinking say that the mayor has looked on with dismay as others with more slender records have vaulted to the top of the Democratic field. The plan, they say, is to point to the fact that de Blasio has for six years presided over one of the most complex organisms in government, and that he has done so as an unapologetic progressive: instituting universal pre-K and after-school programs, keeping crime down while reforming the NYPD and ending stop-and-frisk, keeping the city a place that attracts business and investment even while his administration has raised wages, strengthened the safety net by mandating paid sick leave and kept rent increases in check.

“He has a real record of accomplishment,” said Rebecca Katz, who served as a top adviser to de Blasio in his first term as mayor. “As many kids went through pre-K this year alone as there are people in all of South Bend, Indiana.”

That, of course, is a reference to Buttigieg, the 37-year-old Indiana mayor who has ridden a wave of good publicity to climb into third place in some early primary polling. It is a boomlet that has galled some de Blasio advisers who see the resident of Gracie Mansion dealing with issues that no other person in the race, let alone a mayor of a midsize city, has to deal with: immigration, terrorism, climate change, a ravenous press corps, and the like.

But the mayor will also face questions should he decide to run. He remains under scrutiny for soliciting funds for a nonprofit group from people doing business with the city. Real estate and construction interests have donated heavily to his PAC. The city is facing both homeless and affordability crises.

But the rise of Buttigieg, and for that matter, Donald Trump four years ago, shows that American presidential politics have become about as predictable as a game of Chutes and Ladders. The best bet is to take your turn, spin, and see what happens. Although senators like Bernie Sanders and Elizabeth Warren have staked out the left side of the Democratic Party, supporters of de Blasio’s believe that he has a record of accomplishment more substantive than theirs.

“He’s going to be able to say I am the progressive that has actually gotten shit done,” said one former aide. “It’s that, and then you just hope lightning strikes.”

But running for president is also a chance for the mayor to tell the story of his administration in a way he is unable to at home. De Blasio believes that he will never get a fair shake from the New York City press corps who cover him day in and day out. The relationship between the two started out poorly, with the press accusing the mayor of a lack of transparency and a dismissiveness toward the role of the Fourth Estate, and the mayor accusing the media of playing a game of gotcha in pursuit of clicks. Running for president will give de Blasio a new audience, one less tired of his shtick.

In the early days at least, the “de Blasio for president” campaign is likely to be a top-heavy operation. Most of the people he surrounded himself with in City Hall have since moved on. The consultants who powered his mayoral campaigns — Katz, Bill Hyers, Nick Baldick, Jonathan Rosen, Anna Greenberg, and John Del Cecato all told Politico last month that they are working with other candidates or sitting out 2020. A top adviser from his 2017 reelection campaign, Phil Walzak, is now working in communications at the NYPD, and his longtime spokesman, Eric Phillips, left for a job in the private sector last month. Mike Casca, a former Bernie Sanders 2016 staffer and a top aide who left City Hall for de Blasio’s Fairness PAC last month, has since left the PAC. Two other aides, deputy press secretary Olivia Lapeyrolerie and deputy director of executive operations Alexandra Kopel are taking temporary leave to go work on the PAC as well.

De Blasio hasn’t begun to hire in the early primary states, and will likely struggle to lure top-notch talent, since most of the sought-after staffers have already been snatched up by his rivals, and those that haven’t are unlikely to sign on with someone who has yet to show that his campaign is viable.

But as easy as it is to dismiss de Blasio as someone who must have been power napping in his office the past six months and missed the state of the Democratic primary, once he starts campaigning, the mayor’s political skills are undeniable. In both his citywide race for public advocate and his first race for mayor, he started way down in the polls, but saw the field take shape and correctly strategized how to create space for himself. Of course, he won both easily. Associates expect the mayor to decamp quickly to New Hampshire, where, as a native of Massachusetts, he can boast of some ties to the first-in-the-nation primary state, and to South Carolina, where the Democratic primary electorate is over 55 percent African-American and is currently seen as up for grabs. De Blasio outperformed Bill Thompson, who was vying to be the city’s second black mayor, among black voters in his first race for mayor, in part by relying on his biracial family.

De Blasio’s biggest and earliest test will be reaching the threshold to qualify for the first debate. Candidates have to get at least one percent in three public polls, or receive campaign donations from 65,000 individuals with at least 200 donors apiece in 20 states to get on the stage, and some who have been campaigning for a while, like Booker and New York senator Kirsten Gillibrand, have struggled to meet the donor threshold. A March Monmouth poll gave de Blasio one percent — better than Gillibrand or Washington governor Jay Inslee, but he was also the only Democrat who had a negative favorability rating. It is a belief among de Blasio’s team that he could still mount a viable campaign, even if he were to miss the first debate, which will be crowded with 20 Democrats trying to have their breakout moment.

And de Blasio is a skilled debater, having squared off in front of the klieg lights for both of his races for mayor, but if he can’t reach the threshold, not only will voters not get a chance to see him, but it would serve as a serious embarrassment. With the debates now only seven weeks away, de Blasio faces an uphill climb to get there, one that could have been avoided if he had just made up his mind and jumped in the race earlier.

But for someone who has been determined to operate on his own schedule in City Hall for the past eight years, the waiting game should not have been a surprise.

“So he’s the last person in,” said one former aide. “I don’t know if you have noticed, but timing ain’t exactly his thing.”

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